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Chemical Compound Review

Kiotorphin     (2S)-2-[[(2S)-2-amino-3-(4...

Synonyms: kyotorphin, Tyr-arg, D-Kyotorphin, SureCN28292, CHEMBL273521, ...
 
 
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Disease relevance of Tyr-arg

 

Psychiatry related information on Tyr-arg

  • Cyclo(N-methyl-L-Tyrosine-L-Arginine) (cyclo NMTA), an analogue of kyotorphin, increased the reaction time in the tail-pressure and tail-flick tests [6].
  • The effects of kyotorphin (KTP), a dipeptide (L-Tyr-L-Arg), on the level of sensory attention to stimuli of different modalities in rats and the exploratory behavior in goldfish were investigated [7].
 

High impact information on Tyr-arg

  • Purification of a novel type of calcium-activated neutral protease from rat brain. Possible involvement in production of the neuropeptide kyotorphin from calpastatin fragments [8].
  • Kyotorphin (tyrosine-arginine) synthetase in rat brain synaptosomes [9].
  • The site of action of kyotorphin-induced responses was identified to be on nociceptor endings, because the responses were markedly attenuated by intrathecal pretreatments with Galpha(i1) or Galpha(i2) antisense-oligodeoxynucleotides [10].
  • The antinociceptive effects of all these new Trp(Nps)-containing dipeptides were evaluated after icv administration in mice, and the effects were compared with those of 1b, 2b, Tyr-Arg (Kyotorphin), and Tyr-D-Arg [11].
  • In view of the structure-activity relationships obtained, several similarities between this series of Trp(Nps)-containing dipeptides and that of Kyotorphin analogues have emerged [11].
 

Biological context of Tyr-arg

 

Anatomical context of Tyr-arg

 

Associations of Tyr-arg with other chemical compounds

  • In rat cerebellar cytosol, the binding activity of [3H]NG-nitro-L-arginine (NNA) was inhibited equally by L-arginine (L-Arg), kyotorphin, and L-leucyl-L-Arg (a kyotorphin receptor antagonist) [18].
  • Type II arginase may be an important part of the arginine regulatory system affecting nitric oxide synthase, arginine decarboxylase, kyotorphin synthase, and arginine-glycine transaminase activities and polyamine and proline biosynthesis [19].
  • A putative met-enkephalin releaser, kyotorphin enhances intracellular Ca2+ in the synaptosomes [20].
  • These findings suggest that the nociceptive effect produced by Tyr(NMe)-Arg-OH in subattomol doses occurs via specific interaction with the kyotorphin receptor and that the extraordinary potency observed may result from amplification through local substance P release [21].
  • In the crude soluble extracts from the adrenal glands and spinal cord, kyotorphin was formed by kyotorphin synthetase, and also by the enzymatic processing of the precursor proteins, in the presence of physiological concentrations of L-Tyr and L-Arg in addition to ATP and MgCl2 [16].
 

Gene context of Tyr-arg

  • Low dose of kyotorphin (tyrosine-arginine) induces nociceptive responses through a substance P release from nociceptor endings [22].
  • These results suggest that kyotorphin is degraded to L-Arg by KTPases, which in turn may act as substrate for nNOS [18].
  • Isolation and identification of an analgesic opioid dipeptide kyotorphin (Tyr-Arg) from bovine brain [23].
  • In particular, kyotorphin (Tyr-Arg) completely inhibited Gly-Sar uptake with the K(i) value of 29+/-14 microM [24].
  • The effects of a new endogenous opioid dipeptide (Tyr-Arg), kyotorphin, on single unit activities recorded from the lamina V type neurons in the spinal dorsal horn and the neurons in nucleus reticularis paragigantocellularis (NRPG) of the medulla oblongata were investigated in the rabbit and rat, respectively [25].
 

Analytical, diagnostic and therapeutic context of Tyr-arg

References

  1. The kyotorphin (tyrosine-arginine) receptor and a selective reconstitution with purified Gi, measured with GTPase and phospholipase C assays. Ueda, H., Yoshihara, Y., Misawa, H., Fukushima, N., Katada, T., Ui, M., Takagi, H., Satoh, M. J. Biol. Chem. (1989) [Pubmed]
  2. L-leucyl-L-arginine, naltrindole and D-arginine block antinociception elicited by L-arginine in mice with carrageenin-induced hyperalgesia. Kawabata, A., Nishimura, Y., Takagi, H. Br. J. Pharmacol. (1992) [Pubmed]
  3. A novel method for the synthesis of kyotorphin, Tyr-Arg, and 3H-Tyr-Arg, catalyzed by tyrosyl-tRNA synthetase from Bacillus stearothermophilus. Kitabatake, S., Tsurutani, R., Nakajima, H., Tomita, K., Yoshihara, Y., Ueda, H., Takagi, H., Imahori, K. Pharm. Res. (1987) [Pubmed]
  4. Actions of intracerebroventricular administration of kyotorphin and an analog on thermoregulation in the mouse. Sakurada, T., Sakurada, S., Watanabe, S., Matsumura, H., Kisara, K., Akutsu, Y., Sasaki, Y., Suzuki, K. Peptides (1983) [Pubmed]
  5. Seizure-protecting effects of kyotorphin and related peptides in an animal model of epilepsy. Godlevsky, L.S., Shandra, A.A., Mikhaleva, I.I., Vastyanov, R.S., Mazarati, A.M. Brain Res. Bull. (1995) [Pubmed]
  6. Comparison of the antinociceptive effects of intracerebroventricular injection of kyotorphin, cyclo (N-methyl-Tyr-Arg) and Met-enkephalin in mice. Sakurada, T., Sakurada, S., Watanabe, S., Kawamura, S., Sato, T., Kisara, K., Akutsu, Y., Sasaki, Y., Suzuki, K. Neuropharmacology (1984) [Pubmed]
  7. Effects of L-thyrosyl - L-arginine (kyotorphin) on the behavior of rats and goldfish. Kolaeva, S.G., Semenova, T.P., Santalova, I.M., Moshkov, D.A., Anoshkina, I.A., Golozubova, V. Peptides (2000) [Pubmed]
  8. Purification of a novel type of calcium-activated neutral protease from rat brain. Possible involvement in production of the neuropeptide kyotorphin from calpastatin fragments. Yoshihara, Y., Ueda, H., Fujii, N., Shide, A., Yajima, H., Satoh, M. J. Biol. Chem. (1990) [Pubmed]
  9. Kyotorphin (tyrosine-arginine) synthetase in rat brain synaptosomes. Ueda, H., Yoshihara, Y., Fukushima, N., Shiomi, H., Nakamura, A., Takagi, H. J. Biol. Chem. (1987) [Pubmed]
  10. In vivo signal transduction of nociceptive response by kyotorphin (tyrosine-arginine) through Galpha(i)- and inositol trisphosphate-mediated Ca(2+) influx. Ueda, H., Inoue, M. Mol. Pharmacol. (2000) [Pubmed]
  11. Analgesic dipeptide derivatives. 4. Linear and cyclic analogues of the analgesic compounds arginyl-2-[(o-nitrophenyl)sulfenyl]tryptophan and lysyl-2-[(o-nitrophenyl)sulfenyl]tryptophan. Garcia-López, M.T., González-Muñiz, R., Molinero, M.T., Del Rio, J. J. Med. Chem. (1988) [Pubmed]
  12. Effect of the endogenous analgesic dipeptide, kyotorphin, on transmitter release in sympathetic ganglia. Hirai, K., Katayama, Y. Br. J. Pharmacol. (1985) [Pubmed]
  13. An enkephalin-degrading aminopeptidase from rat brain catalyzes the hydrolysis of a neuropeptide, kyotorphin (L-Tyr-L-Arg). Akasaki, K., Tsuji, H. Chem. Pharm. Bull. (1991) [Pubmed]
  14. Effects of central injection of kyotorphin and L-arginine on oxytocin and vasopressin release and blood pressure in conscious rats. Summy-Long, J.Y., Bui, V., Gestl, S., Koehler-Stec, E., Liu, H., Terrell, M.L., Kadekaro, M. Brain Res. Bull. (1998) [Pubmed]
  15. Mechanism of kyotorphin-induced release of Met-enkephalin from guinea pig striatum and spinal cord. Shiomi, H., Kuraishi, Y., Ueda, H., Harada, Y., Amano, H., Takagi, H. Brain Res. (1981) [Pubmed]
  16. Kyotorphin synthetase activity in rat adrenal glands and spinal cord. Kawabata, A., Muguruma, H., Tanaka, M., Takagi, H. Peptides (1996) [Pubmed]
  17. Kyotorphin has a novel action on rat cardiac muscle. Li, Y., Saito, Y., Suzuki, M., Ueda, H., Endo, M., Maruyama, K. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
  18. Effects of kyotorphin (L-tyrosyl-L-arginine) ON[3H]NG-nitro-L-arginine binding to neuronal nitric oxide synthase in rat brain. Arima, T., Kitamura, Y., Nishiya, T., Taniguchi, T., Takagi, H., Nomura, Y. Neurochem. Int. (1997) [Pubmed]
  19. Cloning and characterization of the human type II arginase gene. Vockley, J.G., Jenkinson, C.P., Shukla, H., Kern, R.M., Grody, W.W., Cederbaum, S.D. Genomics (1996) [Pubmed]
  20. A putative met-enkephalin releaser, kyotorphin enhances intracellular Ca2+ in the synaptosomes. Ueda, H., Yoshihara, Y., Takagi, H. Biochem. Biophys. Res. Commun. (1986) [Pubmed]
  21. An enzymatically stable kyotorphin analog induces pain in subattomol doses. Ueda, H., Inoue, M., Weltrowska, G., Schiller, P.W. Peptides (2000) [Pubmed]
  22. Low dose of kyotorphin (tyrosine-arginine) induces nociceptive responses through a substance P release from nociceptor endings. Inoue, M., Yamada, T., Ueda, H. Brain Res. Mol. Brain Res. (1999) [Pubmed]
  23. Isolation and identification of an analgesic opioid dipeptide kyotorphin (Tyr-Arg) from bovine brain. Shiomi, H., Ueda, H., Takagi, H. Neuropharmacology (1981) [Pubmed]
  24. Functional characterization of brain peptide transporter in rat cerebral cortex: identification of the high-affinity type H+/peptide transporter PEPT2. Fujita, T., Kishida, T., Wada, M., Okada, N., Yamamoto, A., Leibach, F.H., Ganapathy, V. Brain Res. (2004) [Pubmed]
  25. Effects of tyrosyl-arginine (kyotorphin), a new opioid dipeptide, on single neurons in the spinal dorsal horn of rabbits and the nucleus reticularis paragigantocellularis of rats. Satoh, M., Kawajiri, S., Yamamoto, M., Akaike, A., Ukai, Y., Takagi, H. Neurosci. Lett. (1980) [Pubmed]
  26. Regional distribution of a novel analgesic dipeptide kyotorphin (Tyr-Arg) in the rat brain and spinal cord. Ueda, H., Shiomi, H., Takagi, H. Brain Res. (1980) [Pubmed]
  27. Analgesic dipeptide, kyotorphin (Tyr-Arg), is highly concentrated in the synaptosomal fraction of the rat brain. Ueda, H., Tatsumi, K., Shiomi, H., Takagi, H. Brain Res. (1982) [Pubmed]
  28. Effects of a number of short peptides isolated from the brain of the hibernating ground squirrel on the EEG and behavior in rats. Ignat'ev, D.A., Vorob'ev, V.V., Ziganshin, R.K.h. Neurosci. Behav. Physiol. (1998) [Pubmed]
 
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